Ethyl 8-hydroxy-alpha-(2-propynylamino)-5-quinolinepropanoate | 686723-15-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 8-hydroxy-alpha-(2-propynylamino)-5-quinolinepropanoate
• 英文别名: ethyl 3-(8-hydroxyquinolin-5-yl)-2-(prop-2-ynylamino)propanoate
• CAS: 686723-15-9
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: IQZXIKMXXCLFOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  DL-3-(8-hydroxyquinolin-5-yl)alanine ethyl ester 、 3-溴丙炔 在 碳酸氢钠 作用下， 以 二甲基亚砜 为溶剂， 以70%的产率得到Ethyl 8-hydroxy-alpha-(2-propynylamino)-5-quinolinepropanoate
  参考文献：
  名称：

  Design, synthesis, and evaluation of novel bifunctional iron-chelators as potential agents for neuroprotection in Alzheimer’s, Parkinson’s, and other neurodegenerative diseases

  摘要：

  Several novel antioxidant-iron chelators bearing 8-hydroxyoxyquinoline moiety were synthesized, and various properties related to their iron chelation, and neuroprotective action were investigated. All the chelators exhibited strong iron(III) chelating and high antioxidant properties. Chelator 9 (HLA20). having good permeability into K562 cells and moderate selective MAO-B inhibitory activity (IC50 110 muM), displayed the hightest protective effects against differentiated P19 cell death induced by 6-hydroxydopamine. EPR studies suggested that Chelator 9 also act as radical scavenger to directly scavenge hydroxyl radical. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.037

文献信息

• NEUROPROTECTIVE IRON CHELATORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM
  申请人：YOUDIM MOUSSA

  公开号：US20120058945A1

  公开（公告）日：2012-03-08

  Novel iron chelators exhibiting neuroprotective and good transport properties are useful in iron chelation therapy for treatment of a disease, disorder or condition associated with iron overload and oxidative stress, e.g., a neurodegenerative or cerebrovascular disease or disorder, a neoplastic disease, hemochromatosis, thalassemia, a cardiovascular disease, diabetes, an inflammatory disorder, anthracycline cardiotoxicity, a viral infection, a protozoal infection, a yeast infection, retarding aging, and prevention and/or treatment of skin aging and skin protection against sunlight and/or UV light. The iron chelator function is provided by a 8-hydroxyquinoline, a hydroxypyridinone or a hydroxamate moiety. The neuroprotective function is imparted to the compound, e.g., by a neuroprotective peptide. A combined antiapoptotic and neuroprotective function is provided by a propargyl group.

  表现出神经保护和良好输送特性的新型铁螯合剂，可用于治疗与铁过载和氧化应激相关的疾病、障碍或病况，例如神经退行性或脑血管疾病或障碍、肿瘤性疾病、血色病、地中海贫血、心血管疾病、糖尿病、炎症性疾病、蒽环类心肌毒性、病毒感染、原虫感染、酵母感染、延缓衰老以及预防和/或治疗皮肤老化和皮肤对阳光和/或紫外线的保护。铁螯合剂功能由8-羟基喹啉、羟基吡啶酮或羟肟酸基团提供。神经保护功能由神经保护肽等化合物赋予。丙炔基提供了联合抗凋亡和神经保护功能。
• US8058442B2
  申请人：——

  公开号：US8058442B2

  公开（公告）日：2011-11-15
• [EN] NEUROPROTECTIVE IRON CHELATORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM<br/>[FR] CHELATEURS DU FER ET COMPOSITIONS PHARMACEUTIQUES LES RENFERMANT
  申请人：TECHNION RES & DEV FOUNDATION

  公开号：WO2004041151A2

  公开（公告）日：2004-05-21

  Novel iron chelators exhibiting neuroprotective and good transport properties are useful in iron chelation therapy for treatment of a disease, disorder or condition associated with iron overload and oxidative stress, eg. a neurodegenerative or cerebrovascular disease or disorder, a neoplastic disease, hemochromatosis, thalassemia, a cardiovascular disease, diabetes, a inflammatory disorder, anthracycline cardiotoxicity, a viral infection, a protozoal infection, a yeast infection, retarding ageing, and prevention and/or treatment of skin ageing and skin protection against sunlight and/or UV light. The iron chelator function is provided by a 8-hydroxyquinoline, a hydroxypyridinone or a hydroxamate moiety, the neuroprotective function is imparted to the compound e.g. by a neuroprotective peptide, and a combined antiapoptotic and neuroprotective function by a propargyl group.
• Design, synthesis, and evaluation of novel bifunctional iron-chelators as potential agents for neuroprotection in Alzheimer’s, Parkinson’s, and other neurodegenerative diseases
  作者：Hailin Zheng、Lev M. Weiner、Orit Bar-Am、Silvina Epsztejn、Z. Ioav Cabantchik、Abraham Warshawsky、Moussa B.H. Youdim、Mati Fridkin

  DOI：10.1016/j.bmc.2004.10.037

  日期：2005.2

  Several novel antioxidant-iron chelators bearing 8-hydroxyoxyquinoline moiety were synthesized, and various properties related to their iron chelation, and neuroprotective action were investigated. All the chelators exhibited strong iron(III) chelating and high antioxidant properties. Chelator 9 (HLA20). having good permeability into K562 cells and moderate selective MAO-B inhibitory activity (IC50 110 muM), displayed the hightest protective effects against differentiated P19 cell death induced by 6-hydroxydopamine. EPR studies suggested that Chelator 9 also act as radical scavenger to directly scavenge hydroxyl radical. (C) 2004 Elsevier Ltd. All rights reserved.